BRPI0711169A2 - tetrahidropirrolopiridinadionas e seu uso como inibidores de elastase neutrófilo humano - Google Patents
tetrahidropirrolopiridinadionas e seu uso como inibidores de elastase neutrófilo humano Download PDFInfo
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- BRPI0711169A2 BRPI0711169A2 BRPI0711169-0A BRPI0711169A BRPI0711169A2 BR PI0711169 A2 BRPI0711169 A2 BR PI0711169A2 BR PI0711169 A BRPI0711169 A BR PI0711169A BR PI0711169 A2 BRPI0711169 A2 BR PI0711169A2
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- -1 tetrahydropyrrolopyridinediones Chemical class 0.000 title claims description 36
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 title abstract description 31
- 102000052502 human ELANE Human genes 0.000 title abstract description 29
- 239000003591 leukocyte elastase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 201000010099 disease Diseases 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims description 74
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000005647 linker group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000006413 ring segment Chemical group 0.000 claims description 11
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 206010014561 Emphysema Diseases 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical group 0.000 claims description 9
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 229910052705 radium Inorganic materials 0.000 claims description 5
- 229910052701 rubidium Inorganic materials 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 206010006451 bronchitis Diseases 0.000 claims description 4
- 208000007451 chronic bronchitis Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
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- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 101000856746 Bos taurus Cytochrome c oxidase subunit 7A1, mitochondrial Proteins 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 238000012217 deletion Methods 0.000 claims description 2
- 230000037430 deletion Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 206010003645 Atopy Diseases 0.000 claims 2
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- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
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- 201000004681 Psoriasis Diseases 0.000 claims 1
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- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
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- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
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- 239000003112 inhibitor Substances 0.000 abstract description 8
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- 239000000178 monomer Substances 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 78
- 239000000543 intermediate Substances 0.000 description 67
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 51
- 239000000243 solution Substances 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
- 239000000047 product Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000004128 high performance liquid chromatography Methods 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
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- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/55—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug, i.e. a dimer, oligomer or polymer of pharmacologically or therapeutically active compounds
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0608844A GB0608844D0 (en) | 2006-05-04 | 2006-05-04 | Enzyme inhibitors |
| GB0608844.7 | 2006-05-04 | ||
| GB0612544.7 | 2006-06-23 | ||
| GB0612544A GB0612544D0 (en) | 2006-06-23 | 2006-06-23 | Enzyme inhibitors |
| PCT/GB2007/001638 WO2007129060A1 (en) | 2006-05-04 | 2007-05-03 | Tetrahydropyrrolopyrimidinediones and their use as human neutrophil elastase inhibitors |
Publications (1)
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| BRPI0711169A2 true BRPI0711169A2 (pt) | 2011-08-23 |
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| BRPI0711169-0A BRPI0711169A2 (pt) | 2006-05-04 | 2007-05-03 | tetrahidropirrolopiridinadionas e seu uso como inibidores de elastase neutrófilo humano |
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| Country | Link |
|---|---|
| US (1) | US8957082B2 (pl) |
| EP (1) | EP2024367B1 (pl) |
| JP (1) | JP4999920B2 (pl) |
| AT (1) | ATE480543T1 (pl) |
| AU (1) | AU2007246889B2 (pl) |
| BR (1) | BRPI0711169A2 (pl) |
| CA (1) | CA2657956C (pl) |
| CY (1) | CY1111437T1 (pl) |
| DE (1) | DE602007009095D1 (pl) |
| DK (1) | DK2024367T3 (pl) |
| EA (1) | EA018061B1 (pl) |
| IL (1) | IL194843A (pl) |
| MX (1) | MX2008013996A (pl) |
| NO (1) | NO20084502L (pl) |
| NZ (1) | NZ572250A (pl) |
| PL (1) | PL2024367T3 (pl) |
| PT (1) | PT2024367E (pl) |
| SI (1) | SI2024367T1 (pl) |
| WO (1) | WO2007129060A1 (pl) |
| ZA (1) | ZA200809250B (pl) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0302486D0 (sv) | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| US8198288B2 (en) | 2006-05-04 | 2012-06-12 | Pulmagen Therapeutics (Inflammation) Limited | Tetrahydropyrrolopyrimidinediones and their use in therapy |
| DE602007009095D1 (de) | 2006-05-04 | 2010-10-21 | Pulmagen Therapeutics Inflamma | Tetrahydropyrrolopyrimidindione und ihre verwendung als inhibitoren der humanen neutrophilen elastase |
| WO2009013444A1 (en) * | 2007-07-25 | 2009-01-29 | Argenta Discovery Limited | Tetrahydropyrrolopyrimidinediones and their use as human neutrophil elastase inhibitors |
| TW200808763A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
| TW200808771A (en) | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| EP2064184A1 (en) * | 2006-09-04 | 2009-06-03 | AstraZeneca AB | Multimeric heterocyclic compounds useful as neutrophil elastase inhibitors |
| JP2011502982A (ja) | 2007-11-06 | 2011-01-27 | アストラゼネカ・アクチエボラーグ | 好中球エラスターゼの阻害剤としてのある種の２−ピラジノン誘導体およびその使用 |
| WO2009060158A1 (en) * | 2007-11-07 | 2009-05-14 | Argenta Discovery Limited | 4- (4-cyanophenyl) -1- (3-trifluoromethylphenyl) -3,4, 6, 7-tetrahydro-1h-pyrrolo [3, 4- d] pyrimidine-2, 5-dione derivatives and their use as human neutrophil elastase inhibitors |
| GB0721866D0 (en) * | 2007-11-07 | 2007-12-19 | Argenta Discovery Ltd | Pharmaceutical compounds having dual activities |
| WO2009060206A1 (en) * | 2007-11-07 | 2009-05-14 | Argenta Discovery Limited | 3,4,6,7-tetrahydro-1h-pyrrolo[3,4-d]pyrimidine-2,5-diones and their therapeutic use |
| DE102008022521A1 (de) * | 2008-05-07 | 2009-11-12 | Bayer Schering Pharma Aktiengesellschaft | 1,4-Diaryl-pyrimidopyridazin-2,5-dione und ihre Verwendung |
| DE102007061766A1 (de) | 2007-12-20 | 2009-06-25 | Bayer Healthcare Ag | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
| BRPI0821027B8 (pt) | 2007-12-20 | 2021-05-25 | Bayer Ip Gmbh | 4-(4-ciano-2-tioaril)di-hidropirimidinonas para tratamento e/ou prevenção de lesões do pulmão e do sistema cardiovascular, seu processo de preparação e seu uso, e medicamento |
| DE102008052013A1 (de) | 2008-10-17 | 2010-04-22 | Bayer Schering Pharma Aktiengesellschaft | 4-(4-Cyano-2-thioaryl)-dihydropyrimidinone und ihre Verwendung |
| GB0817429D0 (en) * | 2008-09-23 | 2008-10-29 | Argenta Discovery Ltd | Enzyme inhibitors |
| DE102009004197A1 (de) | 2009-01-09 | 2010-07-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch anellierte Diaryldihydropyrimidin-Derivate und ihre Verwendung |
| AU2010209456A1 (en) | 2009-01-30 | 2011-08-18 | Chiesi Farmaceutici S.P.A. | Dimeric pyrrolopyrimidinedione and its use in therapy of respiratory diseases |
| TW201036957A (en) | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| MX2012003644A (es) | 2009-10-02 | 2012-04-30 | Astrazeneca Ab | Compuestos de 2-piridona empleados como inhibidores de la elastasa neutrofila. |
| GB201004178D0 (en) * | 2010-03-12 | 2010-04-28 | Pulmagen Therapeutics Inflamma | Enzyme inhibitors |
| GB201004179D0 (en) * | 2010-03-12 | 2010-04-28 | Pulmagen Therapeutics Inflamma | Enzyme inhibitors |
| DE102010030187A1 (de) | 2010-06-16 | 2011-12-22 | Bayer Schering Pharma Aktiengesellschaft | 4-Cyan-2-sulfonylphenyl)pyrazolyl-substituierte Pyridinone und Pyrazinone und ihre Verwendung |
| CA2848557A1 (en) * | 2011-09-14 | 2013-03-21 | Chiesi Farmaceutici S.P.A. | Tetrahydrotriazolopyrimidine derivatives as human neutrophil elastase inhibitors |
| US20140221335A1 (en) * | 2013-02-06 | 2014-08-07 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9115093B2 (en) | 2013-03-04 | 2015-08-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| KR20160097227A (ko) | 2013-12-16 | 2016-08-17 | 키에시 파르마슈티시 엣스. 피. 에이. | 인간 호중구 엘라스타제 억제제로서 테트라하이드로트리아졸로피리미딘 유도체 |
| USRE47493E1 (en) | 2014-02-20 | 2019-07-09 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9487528B2 (en) | 2014-06-09 | 2016-11-08 | Chiesi Farmaceutici S.P.A. | Compounds |
| US9657015B2 (en) | 2014-07-31 | 2017-05-23 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9290457B2 (en) | 2014-07-31 | 2016-03-22 | Boehringer Ingelheim International Gmbh | Substituted dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9458113B2 (en) | 2014-07-31 | 2016-10-04 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9440930B2 (en) * | 2014-07-31 | 2016-09-13 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| US9475779B2 (en) | 2014-07-31 | 2016-10-25 | Boehringer Ingelheim International Gmbh | Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity |
| CN110981815A (zh) | 2015-03-18 | 2020-04-10 | Ph制药有限公司 | 用于生产化合物的方法 |
| US20220354833A1 (en) | 2019-09-17 | 2022-11-10 | Mereo Biopharma 4 Limited | Alvelestat for use in the treatment of graft rejection, bronchiolitis obliterans syndrome and graft versus host disease |
| DK4106757T3 (da) | 2020-04-16 | 2023-10-23 | Mereo Biopharma 4 Ltd | Fremgangsmåder der involverer neutrofil elastase-inhibitor alvelestat til behandling af luftvejssygdom medieret af alpha-1-antitrypsin-mangel |
| CN118265527A (zh) | 2021-10-20 | 2024-06-28 | 美莱奥生物制药第四有限公司 | 用于治疗纤维化的中性粒细胞弹性蛋白酶抑制剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9626643D0 (en) | 1996-12-21 | 1997-02-12 | Astra Pharma Prod | Compounds |
| PE107899A1 (es) | 1997-09-09 | 1999-11-17 | Glaxo Group Ltd | Derivados de pirrolopirrolona como inhibidores de elastasa leucocitaria |
| US6630476B2 (en) | 2000-07-07 | 2003-10-07 | Bristol-Myers Squibb Pharma Company | Pyrrolo [3,4-d] pyrimidines as corticotropin releasing factor (CRF) antagonists |
| CA2498052C (en) * | 2002-09-10 | 2011-05-17 | Bayer Healthcare Ag | Heterocyclic derivatives |
| KR20050042190A (ko) | 2002-09-10 | 2005-05-04 | 바이엘 헬스케어 아게 | 급성 및 만성 염증성, 허혈성 및 재형성 과정에 대한 치료제로서의 피리미디논 유도체 |
| GB0502258D0 (en) * | 2005-02-03 | 2005-03-09 | Argenta Discovery Ltd | Compounds and their use |
| GB0520743D0 (en) * | 2005-10-12 | 2005-11-23 | Argenta Discovery Ltd | Compounds and their use |
| DE602007009095D1 (de) | 2006-05-04 | 2010-10-21 | Pulmagen Therapeutics Inflamma | Tetrahydropyrrolopyrimidindione und ihre verwendung als inhibitoren der humanen neutrophilen elastase |
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- 2007-05-03 PL PL07732669T patent/PL2024367T3/pl unknown
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- 2007-05-03 JP JP2009508463A patent/JP4999920B2/ja not_active Expired - Fee Related
- 2007-05-03 EA EA200870391A patent/EA018061B1/ru not_active IP Right Cessation
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- 2007-05-03 WO PCT/GB2007/001638 patent/WO2007129060A1/en not_active Ceased
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- 2007-05-03 DK DK07732669.2T patent/DK2024367T3/da active
- 2007-05-03 AT AT07732669T patent/ATE480543T1/de active
- 2007-05-03 BR BRPI0711169-0A patent/BRPI0711169A2/pt not_active IP Right Cessation
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|---|---|
| SI2024367T1 (sl) | 2011-04-29 |
| US8957082B2 (en) | 2015-02-17 |
| PL2024367T3 (pl) | 2011-05-31 |
| IL194843A0 (en) | 2009-08-03 |
| DK2024367T3 (da) | 2011-01-03 |
| CY1111437T1 (el) | 2015-08-05 |
| PT2024367E (pt) | 2010-12-03 |
| EA200870391A1 (ru) | 2009-06-30 |
| NZ572250A (en) | 2011-10-28 |
| AU2007246889B2 (en) | 2011-03-10 |
| JP4999920B2 (ja) | 2012-08-15 |
| AU2007246889A1 (en) | 2007-11-15 |
| EA018061B1 (ru) | 2013-05-30 |
| CA2657956A1 (en) | 2007-11-15 |
| DE602007009095D1 (de) | 2010-10-21 |
| ZA200809250B (en) | 2010-02-24 |
| HK1130794A1 (en) | 2010-01-08 |
| NO20084502L (no) | 2008-11-26 |
| MX2008013996A (es) | 2009-01-14 |
| IL194843A (en) | 2014-04-30 |
| CA2657956C (en) | 2015-01-06 |
| US20120202826A1 (en) | 2012-08-09 |
| JP2009535389A (ja) | 2009-10-01 |
| EP2024367B1 (en) | 2010-09-08 |
| WO2007129060A1 (en) | 2007-11-15 |
| EP2024367A1 (en) | 2009-02-18 |
| ATE480543T1 (de) | 2010-09-15 |
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